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Oahu Vacation Packages

Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cusine. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best Oahu deals on Hawaii vacation packages today!

Fall & Winter Sale
FREE 3-Day Midsize Hertz Car Rental

Minimum 3-night vacation packages
Book by 5/3/20 for travel through 12/14/20

All Deals Include: Round-trip flights, hotel accommodations, taxes and more

Aston Kaanapali Shores

Kaanapali Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Located oceanfront on Kaanapali Beach, this oceanfront full-service condominium resort combines the comfort and convenience of spacious suites with full kitchens and hotel-caliber services.

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The Westin Maui Resort & Spa, Kaanapali

Kaanapali Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Relax beachfront or hang out poolside while you watch vibrant sunsets on this spectacular stretch of famed Ka’anapali Beach.

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Royal Lahaina Resort

Kaanapali Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

This unique resort set along Kaanapali Beach offers natural beauty, traditional Hawaiian ambiance and attentive service.

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Grand Wailea, A Waldorf Astoria Resort

Wailea, Maui Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

This luxury Hilton beachfront resort offers spacious rooms, 9 pools, 3-story tube slide, spa, fine dining with championship golf nearby.

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Fairmont Kea Lani, Maui

Wailea, Maui Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

Maui's only all-suite and villa luxury oceanfront resort features elegant accommodations with sophisticated amenities in the upscale Wailea resort area.

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Sheraton Maui Resort & Spa

Kaanapali Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

This oceanfront resort in the heart of Kaanapali, Maui features recently renovated rooms and suites ideal for honeymoons.

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Kaanapali Alii

Kaanapali Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

Beachfront property combining the spaciousness and convenience of a luxury condominium with the amenities of a refined resort hotel.

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Ka'anapali Beach Hotel

Kaanapali Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

This beautiful hotel is set amid tropical gardens and features traditional Hawaiian touches.

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Wailea Beach Resort - Marriott, Maui

Wailea, Maui Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

This magnificent resort on 22 oceanfront acres on Maui's sunny side has been transformed to embrace the beauty of its natural surroundings.

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Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea, Maui Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

This chic and vibrant resort features luxurious accommodations on a prime location on Mokapu Beach.

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Hawaii - Hot Deals FREE 3-Day Hertz Car Rental offer: Valid on new bookings made 03/02/2020 - 05/03/2020 for travel 03/02/2020 - 12/14/2020. Minimum 3 nights’ hotel accommodation at participating resort and roundtrip airfare required. Bookings receive FREE a 3-day midsize car rental; additional car rental days may be added at additional rate. Value of 3-day midsize car rental may be applied to upgraded car classes, but may not be redeemed for cash or discounted off the vacation package price. Age restrictions may apply for car rental.

Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]